JP3694065B2 - 環状Ｓ−α−アミノカルボン酸およびＲ−α−アミノカルボキサミドの生物工学的製造方法 - Google Patents
環状Ｓ−α−アミノカルボン酸およびＲ−α−アミノカルボキサミドの生物工学的製造方法 Download PDFInfo
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- JP3694065B2 JP3694065B2 JP14068495A JP14068495A JP3694065B2 JP 3694065 B2 JP3694065 B2 JP 3694065B2 JP 14068495 A JP14068495 A JP 14068495A JP 14068495 A JP14068495 A JP 14068495A JP 3694065 B2 JP3694065 B2 JP 3694065B2
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- Prior art keywords
- aminocarboxamide
- microorganism
- formula
- general formula
- aminocarboxylic acid
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- Expired - Fee Related
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- 125000004122 cyclic group Chemical group 0.000 title abstract description 3
- 238000011138 biotechnological process Methods 0.000 title description 2
- 244000005700 microbiome Species 0.000 claims abstract description 46
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 102000004190 Enzymes Human genes 0.000 claims abstract description 9
- 108090000790 Enzymes Proteins 0.000 claims abstract description 9
- 239000001963 growth medium Substances 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 16
- XIMBESZRBTVIOD-UHFFFAOYSA-N piperidine-2-carboxamide Chemical compound NC(=O)C1CCCCN1 XIMBESZRBTVIOD-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- IVXQBCUBSIPQGU-UHFFFAOYSA-N piperazine-1-carboxamide Chemical compound NC(=O)N1CCNCC1 IVXQBCUBSIPQGU-UHFFFAOYSA-N 0.000 claims description 12
- 241000588747 Klebsiella pneumoniae Species 0.000 claims description 11
- 230000036983 biotransformation Effects 0.000 claims description 11
- 241000589540 Pseudomonas fluorescens Species 0.000 claims description 10
- 241000589776 Pseudomonas putida Species 0.000 claims description 10
- 241000588748 Klebsiella Species 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- RIOBEGOHZRAHCD-UHFFFAOYSA-N 4-methylpiperidine-2-carboxamide Chemical compound CC1CCNC(C(N)=O)C1 RIOBEGOHZRAHCD-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 16
- 239000000284 extract Substances 0.000 abstract description 5
- 235000008206 alpha-amino acids Nutrition 0.000 abstract 6
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229940088598 enzyme Drugs 0.000 description 7
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- 239000000126 substance Substances 0.000 description 6
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- HXEACLLIILLPRG-RXMQYKEDSA-N D-pipecolic acid Chemical compound OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 4
- 201000008225 Klebsiella pneumonia Diseases 0.000 description 4
- -1 Lysine carboxamide Chemical class 0.000 description 4
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- VLJNHYLEOZPXFW-SCSAIBSYSA-N (2r)-pyrrolidine-2-carboxamide Chemical compound NC(=O)[C@H]1CCCN1 VLJNHYLEOZPXFW-SCSAIBSYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 3
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 3
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- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
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- 235000019750 Crude protein Nutrition 0.000 description 2
- 101001009252 Homo sapiens 2-hydroxyacyl-CoA lyase 1 Proteins 0.000 description 2
- VLJNHYLEOZPXFW-BYPYZUCNSA-N L-prolinamide Chemical class NC(=O)[C@@H]1CCCN1 VLJNHYLEOZPXFW-BYPYZUCNSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 241000588756 Raoultella terrigena Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
- 239000006916 nutrient agar Substances 0.000 description 2
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- 239000000758 substrate Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- WOWNQYXIQWQJRJ-UHFFFAOYSA-N (3,4,5-triacetyloxy-6-isothiocyanatooxan-2-yl)methyl acetate Chemical compound CC(=O)OCC1OC(N=C=S)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O WOWNQYXIQWQJRJ-UHFFFAOYSA-N 0.000 description 1
- NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical compound C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 description 1
- SNPTUOFTDDDSOA-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline-2-carboxamide Chemical compound C1CCCC2NC(C(=O)N)CCC21 SNPTUOFTDDDSOA-UHFFFAOYSA-N 0.000 description 1
- KNRBIDGVVFRFLZ-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoxaline-2-carboxamide Chemical compound C1CCCC2NC(C(=O)N)CNC21 KNRBIDGVVFRFLZ-UHFFFAOYSA-N 0.000 description 1
- FTAPDLRVRYASRX-UHFFFAOYSA-N 1,3-oxazolidine-2-carboxamide Chemical class NC(=O)C1NCCO1 FTAPDLRVRYASRX-UHFFFAOYSA-N 0.000 description 1
- YDGXLVKDGGLWPF-UHFFFAOYSA-N 1,3-thiazolidine-2-carboxamide Chemical compound NC(=O)C1NCCS1 YDGXLVKDGGLWPF-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- 108090000531 Amidohydrolases Proteins 0.000 description 1
- 102000004092 Amidohydrolases Human genes 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 238000003794 Gram staining Methods 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 229930182821 L-proline Natural products 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000008430 aromatic amides Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 210000004671 cell-free system Anatomy 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 239000012228 culture supernatant Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- NTFOMPCTOJCWEK-UHFFFAOYSA-N imidazolidine-1-carboxamide Chemical class NC(=O)N1CCNC1 NTFOMPCTOJCWEK-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- LXWHOYSOMNNXRS-UHFFFAOYSA-N pyrazolidine-1-carboxamide Chemical class NC(=O)N1CCCN1 LXWHOYSOMNNXRS-UHFFFAOYSA-N 0.000 description 1
- 238000012113 quantitative test Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960002784 thioridazine Drugs 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
- C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/22—Klebsiella
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/38—Pseudomonas
- C12R2001/39—Pseudomonas fluorescens
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/38—Pseudomonas
- C12R2001/40—Pseudomonas putida
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/852—Klebsiella
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/874—Pseudomonas
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/874—Pseudomonas
- Y10S435/876—Pseudomonas fluorescens
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/874—Pseudomonas
- Y10S435/877—Pseudomonas putida
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/878—Rhizobium
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH181394 | 1994-06-09 | ||
| CH2231/94-9 | 1994-07-13 | ||
| CH223194 | 1994-07-13 | ||
| CH1813/94-4 | 1994-07-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0856652A JPH0856652A (ja) | 1996-03-05 |
| JP3694065B2 true JP3694065B2 (ja) | 2005-09-14 |
Family
ID=25688747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14068495A Expired - Fee Related JP3694065B2 (ja) | 1994-06-09 | 1995-06-07 | 環状Ｓ−α−アミノカルボン酸およびＲ−α−アミノカルボキサミドの生物工学的製造方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US5622846A (cs) |
| EP (1) | EP0686698B1 (cs) |
| JP (1) | JP3694065B2 (cs) |
| AT (1) | ATE199743T1 (cs) |
| CA (1) | CA2150526C (cs) |
| CZ (2) | CZ282098B6 (cs) |
| DE (1) | DE59509085D1 (cs) |
| DK (1) | DK0686698T3 (cs) |
| ES (1) | ES2155104T3 (cs) |
| PT (1) | PT686698E (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ213199A3 (cs) * | 1996-12-16 | 1999-11-17 | Lonza Ag | Mikroorganismy, enzymy a způsob výroby derivátů D-prolinu |
| CA2299324A1 (en) * | 1997-08-11 | 1999-02-18 | Lonza Ag | Method for producing cyclic .alpha.-amino acids free from enantiomers or their n-protected derivatives by means of a d-specific aminoacylase |
| CA2341554A1 (en) * | 1998-08-26 | 2000-03-09 | Klaus Heinzmann | Process for the preparation of (2r)-piperidine derivatives |
| US9453251B2 (en) | 2002-10-08 | 2016-09-27 | Pfenex Inc. | Expression of mammalian proteins in Pseudomonas fluorescens |
| JP5602336B2 (ja) | 2004-01-16 | 2014-10-08 | フェネックス インコーポレイテッド | シュードモナス・フルオレッセンスにおける哺乳動物タンパク質の発現 |
| CN101031655A (zh) | 2004-07-26 | 2007-09-05 | 陶氏环球技术公司 | 通过株工程改进蛋白表达的方法 |
| US8338142B2 (en) | 2007-02-19 | 2012-12-25 | Kaneka Corporation | Method for producing optically active 3-aminopiperidine or salt thereof |
| US8367412B2 (en) * | 2007-02-23 | 2013-02-05 | Kwansei Gakuin Educational Foundation | Protein crystallizing agent and method of crystallizing protein therewith |
| CA2964910C (en) | 2007-04-27 | 2018-01-09 | Pfenex Inc. | Method for rapidly screening microbial hosts to identify certain strains with improved yield and/or quality in the expression of heterologous proteins |
| US9580719B2 (en) | 2007-04-27 | 2017-02-28 | Pfenex, Inc. | Method for rapidly screening microbial hosts to identify certain strains with improved yield and/or quality in the expression of heterologous proteins |
| CA2865237C (en) | 2012-02-28 | 2017-08-15 | Marrone Bio Innovations, Inc. | Control of phytopathogenic microorganisms with pseudomonas sp. and substances and compositions derived therefrom |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU74142A1 (cs) * | 1976-01-08 | 1977-07-22 | ||
| JPS6387998A (ja) * | 1986-09-30 | 1988-04-19 | Mitsubishi Gas Chem Co Inc | Ｄ−α−アミノ酸の製造法 |
| ES2051892T3 (es) * | 1987-08-17 | 1994-07-01 | Novo Industri As | Procedimiento para preparar productos quimicos organicos. |
| JPH01215297A (ja) * | 1988-02-23 | 1989-08-29 | Mitsubishi Gas Chem Co Inc | Ｌ−α−アミノ酸の製造法 |
| DK314989A (da) * | 1988-06-27 | 1989-12-28 | Asahi Chemical Ind | Fremgangsmaade til fremstilling af optisk aktive alfa-substituerede organiske syrer, samt mikroorganismer og enzymer anvendelige ved fremgangsmaaden |
| EP0383403A1 (en) * | 1989-02-16 | 1990-08-22 | Stamicarbon B.V. | Process for preparation of organic chemicals |
| NL9100038A (nl) * | 1991-01-11 | 1992-08-03 | Stamicarbon | Enzym-gekatalyseerde bereiding van optisch aktieve carbonzuren. |
-
1995
- 1995-05-30 CA CA002150526A patent/CA2150526C/en not_active Expired - Fee Related
- 1995-06-07 DE DE59509085T patent/DE59509085D1/de not_active Expired - Lifetime
- 1995-06-07 PT PT95108740T patent/PT686698E/pt unknown
- 1995-06-07 JP JP14068495A patent/JP3694065B2/ja not_active Expired - Fee Related
- 1995-06-07 ES ES95108740T patent/ES2155104T3/es not_active Expired - Lifetime
- 1995-06-07 DK DK95108740T patent/DK0686698T3/da active
- 1995-06-07 EP EP95108740A patent/EP0686698B1/de not_active Expired - Lifetime
- 1995-06-07 US US08/478,960 patent/US5622846A/en not_active Expired - Lifetime
- 1995-06-07 AT AT95108740T patent/ATE199743T1/de active
- 1995-06-08 CZ CZ951507A patent/CZ282098B6/cs not_active IP Right Cessation
- 1995-06-08 CZ CZ96668A patent/CZ282337B6/cs not_active IP Right Cessation
-
1996
- 1996-03-12 US US08/614,345 patent/US5766893A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE59509085D1 (de) | 2001-04-19 |
| CA2150526A1 (en) | 1995-12-10 |
| JPH0856652A (ja) | 1996-03-05 |
| ATE199743T1 (de) | 2001-03-15 |
| US5766893A (en) | 1998-06-16 |
| PT686698E (pt) | 2001-08-30 |
| CZ282337B6 (cs) | 1997-06-11 |
| EP0686698A2 (de) | 1995-12-13 |
| EP0686698B1 (de) | 2001-03-14 |
| CA2150526C (en) | 2005-11-15 |
| CZ66896A3 (en) | 1996-12-11 |
| DK0686698T3 (da) | 2001-04-17 |
| CZ282098B6 (cs) | 1997-05-14 |
| EP0686698A3 (de) | 1997-05-02 |
| CZ150795A3 (en) | 1996-05-15 |
| US5622846A (en) | 1997-04-22 |
| ES2155104T3 (es) | 2001-05-01 |
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